Abstract
Novel biologically significant manganese(II) complexes with four monobasic bidentate ligands L1H [2-(5-fluoro-2-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarboxamide], L2H [2-(5-fluoro-2-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarbothioamide], L3H [2-(5-bromo-2-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarboxamide] and L4H [2-(5-bromo-2-dihydro-2-oxo-1H-indol-3-ylidene)hydrazinecarbothioamide] were synthesized by complexation of the ligands with MnCl2·4H2O in 1: 1 and 1: 2 molar ratios in methanol. The Schiff base ligands and complexes were characterized by elemental analyses, melting points, molecular weights, IR, 1H and 13C NMR, UV–Vis, EPR, and mass spectra, as well as X-ray powder diffraction patterns. Based on the spectral data, a tetrahedral geometry was proposed for all the synthesized metal complexes. The ligands and complexes were tested in vitro against bacteria (Escherichia coli and Staphylococcus aureus) and fungi (Fusarium semitectum and Aspergillus flavus) to show that they were active against all the microbial strains examined, and the metal complexes were more active in comparison with the ligands. DNA cleavage activity of the complexes was examined by gel electrophoresis.
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Fahmi, N. and Singh, R.V., Transition Met. Chem., 1994, vol. 19, p. 453. doi 10.1007/BF0a0139327
Türkkan, B., Sariboga, B., and Sariboga, N., Transition Met. Chem., 2011, vol. 36, p. 679. doi 10.1007/s11243- 011-9518-7
Singh, K., Barwa, M. S., and Tyagi, P., Eur. J. Med. Chem., 2006, vol. 41, p. 147. doi 10.1016/j.ejmech.2005.06.006
Majumder, A., Rosair, G. M., Mallick, A., Chattopadhyay, N., and Mitra, S., Polyhedron, 2006, vol. 25, p. 1753. doi 10.1016/j.poly.2005.11.029
Freiria, A., Bastida, R., Valencia, L., Macias, A., and Lodeiro, C., Inorg. Chim. Acta., 2006 vol. 359, p. 2383. doi 10.1016/j.ica.2005.12.055
Chohan, Z.H., Rauf, A., and Supuran, C.T., Met. Based Drugs, 2001, vol. 8, p. 287. doi 10.1155/MBD.2002.287
Osowale, A., Kolawale, G.A., and Fagade, O.E., J. Coord. Chem., 2008, vol. 67, p. 1046. doi 10.1080/00958970701482446
Shamsipur, M., Yousefi, M., Hosseini, M., Ganjali, M., Sharghi, H., and Naeimi, H.A., Anal. Chem., 2001, vol. 73, p. 2869. doi 10.1021/ac001449d
Genin, J.M., Biles, C., Keiser, J.B., Poppe, S.M, Swaney, S.M., Tarpley, W.G., Romero, D.L., and Yage, Y.., J. Med. Chem., 2000, vol. 43, p. 1034. doi 10.1021/jm990383f
Nishat, N., Khan, S. A., Parveen, S., and Rasool, R., J. Coord. Chem., 2010, vol. 63, p. 3944. doi 10.1080/00958972.2010.526207
Somogyi, L., Bull. Chem. Soc. Jpn., 2001, vol. 74, p. 873. doi 10.1246/bcsj.74.873
Nejo, A.A., Kolawole, G.A., Dumbele, M.C., and Opoku, A.R., J. Coord. Chem., 2010, vol. 63, p. 4367. doi 10.1080/00958972.2010.539684
Yang, M., Zhang, Y.H., Li, M.X., Lu, Y.L., and Zhang, N., J. Coord. Chem., 2013, vol. 66, p. 3327. doi 10.1080/00958972.2013.834333
Bal, T. R., Anand, B., Yogeeswari, P., and Sriram, D., Bioorg. Med. Chem. Lett., 2005, vol. 15, p. 4451. doi 10.1016/j.bmcl.2005.07.046
Pandeya, S.N. and Sriram, D., Acta. Pharm. Turc., 1998, vol. 40, p. 33.
Bacchi, A., Carcelli, M., Pelagatti, P., Pelizzi, G., Rodriguez Arguelles, M.C., Rogolino, D., Solinas, C., and Zani, F., J. Inorg. Biochem., 2005, vol. 99, p. 397. doi 10.1016/j.jinorgbio.2004.10.008
Cerchiaro, G., Aquilano, K., Filomeni, G., Rotilio, G., Ciriolo, M.R., and Ferriera, A.M.D.C., J. Inorg. Biochem., 2005, vol. 99 p. 1433. doi 10.1016/j.jinorgbio.2005.03.013
Verma, M., Pandeya, S.N., Singh, K.N., and Stables, J.P., Acta. Pharm., 2004, vol. 54, p. 49.
Jarrahpour, A., Khalili, D., Clercq, E D., Salmi, C., and Brunel, J.M., Molecules, 2007, vol. 12, p. 1720. doi 10.3390/12081720
Rainsford, K.D. and Whitehouse, M.W., J. Pharm. Pharmacol., 1976, vol. 28, p. 83. doi 10.1111/j.2042- 7158.1976.tb04035.x
Ferrari, M.B., Capacchi, S., Bisceglie, F., Pelosi, G., and Tarasconi, P., Inorg. Chim. Acta., 2001, vol. 312, p. 81. doi 10.1016/S0020-1693(00)00339-X
Singh, L., Mohan, G., Prashar, R. K., Tripathi, S.P., and Sharma, R.C., Curr. Sci., 1986, vol. 55, p. 846.
Elsome, A.M., Hamilton-Miller, J.M.T., Brumfitt, W., and Noble, W.C., J. Antimicrob. Chemother., 1996, vol. 37, p. 911. doi 10.1093/jac/37.5.911
Badwaik, V.B., Deshmukh, R.D., and Aswar, A.S., J. Coord. Chem., 2009, vol. 62, p. 2037. doi 10.1080/00958970902741244
Li, Y., Wu, Y., Zhao, J., and Yang, P., J. Inorg. Biochem. 2007 vol. 101, p. 283. doi 10.1016/j.jinorgbio.2006.10.004
Zhang, N., Fan, Y.H., Bi, C.F., Zuo, J., Zhang, P.F., Zhang, Z.Y., and Zhu, Z., J. Coord. Chem., 2013, vol. 66, p. 1933. doi 10.1080/00958972.2013.796039
Wang, X.L., Chao, H., Hong, L., Hong, X.L., Nian, Ji.L., and Yuan, Li.X., J. Inorg. Biochem., 2004, vol. 98, p. 423. doi 10.1016/j.jinorgbio.2003.12.006
Patil, S.A, Naik, V.H., Kumar, A., Kulkarni, D., Kamble, U.K., Bagihalli, G.B., and Badami, P.S., J. Coord. Chem., 2010, vol. 63, p. 688. doi 10.1016/j.jinorgbio.2003.12.006
Raman, N., Jeyamurugan, R., Rani, R.U., Baskaran, T., and Mitu, L., J. Coord. Chem., 2010, vol. 63, p. 1629. doi 10.1080/00958972.2010.485643
Bagihalli, G.B. and Patil, S.A., J. Coord. Chem., 2009, vol. 62, p. 1690. doi 10.1080/00958970802668851
Barve, V., Ahmed, F., Adsule, S., and Banerjee, S., J. Med. Chem., 2006, vol. 49, p. 3800. doi 10.1021/jm051068y
Saglam, N., Colak, A., Serbest, K., Dülger, S., Güner, S., Karaböcek, S., and Beldüz, A.O., Bio. Metals., 2002, vol. 15, p. 357. doi 10.1023/A:1020228723299
Refat, M.S., El-Deen, I.M., Anwer, Z.M., and El-Ghol, S., J. Coord. Chem., 2009, vol. 62, p. 1709. doi 10.1080/00958970802684205
Gupta, K.C. and Sutar, A.K., Coord Chem Rev., 2008, vol. 252, p. 1420. doi 10.1016/j.ccr.2007.09.005
Zhou, Y. and Peng, J.N., J. Coord. Chem., 2013, vol. 15, p. 2597. doi 10.1080/00958972.2013.811495
Cozzi, P.G., Chem. Soc. Rev., 2004, vol. 33, p. 410. doi 10.1039/B307853C
Fahmi, N., Sharma, D.K., and Singh, R.V., Synth. React. Inorg. Met. Org. Chem., 1994, vol. 24, p. 377. doi 10.1080/00945719408000118
Joseph, J. and Mehta, B.H. Russ. J. Coord. Chem., 2007, vol. 33, p. 124. doi 10.1134/S1070328407020091
Saxena, C., Bhardwaj, N. C., Singh, D., and Singh, R.V., Synth. React. Inorg. Met. Org. Chem., 1993, vol. 23, p. 1391. doi 10.1080/15533179308016694
Raman, N., Thalamuthu, S., Raja, J.D., Neelakandan, M.A., and Banerjee, S., J. Chil. Chem. Soc., 2008, vol. 53(1), p. 1450. doi 10.4067/S0717-97072008000100025
Sampath, K. and Jayabalakrishnan, C., J. Environ. Nanotechnol., 2013, vol. 2(4), p. 34. doi 10.13074/jent.2013.12.132043
Vogel, A.I., A Textbook of Organic Quantitative Analysis, London, 2004, 5th ed.
Makode, J.T. and Aswar, A.S., Indian J. Chem., 2004, vol. 43A, p. 2120. http://nopr.niscair.res.in/handle/123456789/20435.
Vogel, A.I., A Textbook of Quantitative Chemical Analysis, London, 2006, 6th ed.
Zahid, H., Chohan, M., and Arif, M.S., Appl. Organomet. Chem., 2007, vol. 21, p. 294. doi 10.1002/aoc.1200
Raman, N., Raja, J. D., Sakthivel, A., J. Chem. Sci., 2007, vol. 119, p. 303. doi 10.1007/s12039-007-0041-5
Arish, D. and Nair, M.S., J. Coord. Chem., 2010, vol. 63, p. 1619. doi 10.1080/00958972.2010.483729
Kapoor, P., Singh, R.V., and Fahmi, N., J. Coord. Chem., 2012, vol. 65(2), p. 262. doi 10.1080/00958972.2011.649265
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Sharma, S., Meena, R., Satyawana, Y. et al. Manganese(II) complexes of biological relevance: Synthesis and spectroscopic characterization of novel manganese(II) complexes with monobasic bidentate ligands derived from halo-substituted 1H-indole-2,3-diones. Russ J Gen Chem 86, 2807–2816 (2016). https://doi.org/10.1134/S1070363216120446
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DOI: https://doi.org/10.1134/S1070363216120446